研究業績 (2000年以降) 
Resarch results

1. 炭素-窒素不斉軸を有するアトロプ異性キナゾリノンの化学

佐藤 梓，藤本裕貴，北川 理

有機合成化学協会誌 81(10) 978-987 (2023) 

2.  Chirality Transfer Intramolecular Pauson-Khand Reaction with N–C Axially Chiral Sulfonamides  bearing an Ene-Yne Structure.

Kasahara, R.; Toyoda, T.; Fukasawa, S. Takeuchi, A. Sato, A. Hori, A. Kitagawa, O.

Org. Lett. 25 (40) 7390-7394 (2023) （https://doi.org/10.1021/acs.orglett.3c02893）

3.  Synthesis of Isotopic Atropisomeres Based on 12C/13C Discrimination.

Senda, R.; Watanabe, Y.; Miwa, S. Sato, A. Kitagawa, O.

J. Org. Chem. 88 (13) 9579 (2023) （https://doi.org/10.1021/acs.joc.3c01004）

4.  Synthesis of Isotopic Atropisomeres Based on 12C/13C Discrimination.

Senda, R.; Watanabe, Y.; Miwa, S. Sato, A. Kitagawa, O.

J. Org. Chem. 88 (13) 9579 (2023) （https://doi.org/10.1021/acs.joc.3c01004）

5.  Catalytic Enatioselective Synthesis of N-C Axially Chiral N-(2,6-Disubstituted-phenyl)sulfonamides through Chiral Pd-Catalyzed N-Allylation.

Fukasawa, S.; Toyoda, T.; Kasahara, R.; Nakamura, C.; Kikuchi, Y.; Hori, A.; Richards, G. J.; Kitagawa, O.

Molecules（Special Issue on Atroposelective Synthesis of Novel Axially Chiral Molecules）27 (22), 7819 (2022) 

https://doi.org/10.3390/molecules27227819

6.   Asymmetric Synthesis of Isotopic Atropisomers based on ortho-CH3/CD3 Discrimination and Their Structural Properties .

Miwa, S.; Senda, R.; Saito, K.; Sato A.; Nakamura, Y.; Kitagawa, O.

J. Org. Chem. 87 (21), 13501-13507 (2022)  https://doi.org/10.1021/acs.joc.2c02185     Featured Articleに選定

7.  Rotational Behavior of N-(5-Substituted-pyrimidin-2-yl)anilines: Relayed Electronic Effect in Two N–Ar Bond Rotations.

Homma, D.; Taketani, S.; Shirai, T.; Caytan, E.; Roussel, C.; Elguero, J.; Alkorta, I. Kitagawa, O.

J. Org. Chem. 87 (12), 8118 (2022) https://doi.org/10.1021/acs.joc.2c00845  

8. Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives.

Matsui, R.; Niijima, E. Imai, T.; Kobayashi, H.; Hori, A.; Sato, A.; Nakamura, Y.; Kitagawa, O.

Molecules, 27 (7), 2369 (2022) doi: https://www.mdpi.com/1420-3049/27/7/2369  

9. Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination

Saito, K.; Miwa, S.; Iida, A.; Fujimoto, Y.; Caytan, E.; Roussel, C.; Kitagawa, O.
Org. Lett. 23 (19), 7492-7496 (2021)  

10. Chiral Pd-Catalyzed Enantioselective Syntheses of Various N-C Axially Chiral Compounds and Their Synthetic Application.

Kitagawa, O.
Acc. Chem. Res. 54 (3), 719-730 (2021)    Top 1% Highly Cited Paper in 2021-2022 (Web of Science) 
 

11. Thionation of Optically Pure N-C Axially Chiral Quinazolin-4-one Derivatives with Lawesson’s Reagent.

Niijima, E.; Imai, T.; Suzuki, H.; Fujimoto, Y.; Kitagawa, O.

J. Org. Chem. 86 (1), 709-715 (2021) 

12. Study on Rotational Stability of 2-Aryl-3-(2-Fluorophenyl)Quinazolin-4-One Derivatives.

Iida, A.; Saito, K.; Asada, N.; Fujimoto, Y.; Kitagawa, O.

Heterocycles (Special Issue in honor of Professor Yasuyuki Kita on 77th birthday), 103, 183-189 (2021).

13. Relayed Proton Brake in N-Pyridyl-2-iso-Propylaniline Derivatives: Two Brakes with One Proton.

Furukawa, G.; Shirai, T.; Homma, Y.; Caytan, E.; Vanthuyne, N.; Farran, D. Kitagawa O.

J. Org. Chem. 85 (7), 5109-5113 (2020).

14. Catalytic Enantioselective Synthesis of N−C Axially ChiralSulfonamides through Chiral Palladium-Catalyzed N‑Allylation.

Kikuchi, Y.; Nakamura, C.; Matsuoka, M.; Asami, R.; Kitagawa, O.

J. Org. Chem. 84 (12), 8112-8120 (2019).

15. Chirality-dependent Halogen Bonds in Axially Chiral Quinazolin-4-one Derivatives bearing ortho-Halophenyl Groups.

Imai, T.; Niijima, E.; Terada, S.; Wzorek, A.; Soloshonok, V. A.; Hori, A.; Kitagawa, O.

CrysEngComm. 21 (22), 3385-3389 (2019).

16. N-C Axially Chiral Compounds with an ortho-Fluoro Substituents and Steric Discrimination between Hydrogen and Fluorine Atoms Based on a Diastereoselective Model Reaction.

Iida, A.; Matsuoka, M.; Hasegawa, H.; Vanthuyne, N.; Farran, D.; Roussel, C.; Kitagawa, O.

J. Org. Chem. 84 (6), 3169-3175 (2019).

17. The Self-disproportionation of Enantiomers (SDE) of α-Amino acids Derivatives: Facets of Steric and Electronic Properties.

Hosaka, T.; Imai, T.; Wzorek, A,; Marcinkowska, M.; Kolbus, A.; Kitagawa, O.; Soloshonol, V. A.; Klika, K. D.

Amino Acids, 51 (2), 283-294 (2019).

18. α-Alkylation of N-C Axially Chiral Quinazolinone Derivatives Bearing Various ortho-Substituted Phenyl Groups: Relation between Diastereoselectivity and ortho-Substituent.

Matsuoka, M.; Iida, A.; Kitagawa, O.

Synlett (Cluster on atropisomeric compounds), 29 (16), 2126-2130 (2018).

19. N-C Axially Chiral Anilines: Electronic Effect on Barrier to Rotation and A Remote Proton Brake

Iwasaki, Y.; Morisawa, R.; Yokojima, S.; Hasegawa, H.; Roussel, C.; Vanthuyne, N.; Caytan, E.; Kitagawa, O.

Chem. Eur. J. 24 (17), 4453-4458 (2018).

20. 常温でも配座異性体が分離可能な2,4,6-tri-tert-ブチルアニリドの化学

乙武信敬，北川　理

有機合成化学協会誌，76 (6), 575-583 (2018)

21. The self-disproportionation of enantiomers (SDE): a menace or an opportunity?

Jianlin Han, Osamu Kitagawa, Alicja Wzorek, Karel D. Klika, and Vadim A. Soloshonok

Chem. Sci., 9 (7), 1718-1739 (2018)

22. Possible case of Halogen Bond-Driven Self-Disproportionation of Enantiomers by Achiral Chromatography

Terada, S.; Hirai, M.; Honzawa, A.; Kitagawa, O.; Kamizela, A.; Wzorek, A.; Soloshonok, V. A.

Chem. Eur. J. 23 (58), 14631-14638 (2017).

23. Diastereoselective α-Alkylation of Metallo Enamines Generated from N-C axially Chiral Mebroqualone Derivatives

Matsuoka, M.; Goto, M.; Wzorek, A.; Soloshonok, V. A.; Kitagawa, O.

Org. Lett. 19 (10) 2650-2653 (2017). Synfacts誌にハイライト.

24. Specific Reactivity of 2,4,6-Tri-tert-butylanilide Anions and Its Application to Benzylation Reagent

Yamada, T.; Tsukagoshi, S.; Kitagawa, O.

Tetrahedron Lett. 58 (4) 317-320 (2017)

25. Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization

Hirai, M.; Terada, S.; Yoshida, H.; Ebine, K.; Hirata, T.; Kitagawa, O.

Org. Lett. 18 (21) 5700-5703 (2016).

26. Enantioselective Synthesis of N-C Axially Chiral Indoles through Chiral Palladium-catalyzed 5-Endo-hydroaminocyclization

Morimoto, Y.; Shimizu, S.; Mokuya, A.; Ototake, N.; Saito, A.; Kitagawa, O.

Tetrahedron (Special issue on axial chirality) 72 (34) 5221-5229 (2016).

27. Chiral additive induced self-disproportionation of enantiomers under MPLC conditions: Preparation of enantiomerically pure samples of 1-(aryl)ethylamines from racemates.

Goto, M.; Tateishi, K.; Ebine, K.; Soloshonok, V. A. Roussel, C.; Kitagawa, O.

Tetrahedron: Asymmetry 27 (7) 317-321 (2016).

28. Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives.

Hirata, T.; Takahashi, I.; Suzuki, Y.; Yoshida, H.; Hasegawa, H.; Kitagawa, O.

J. Org. Chem. 81 (1) 318-323 (2016). Synfacts誌にハイライト.

29. Synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to acid-accelerated molecular rotor

Suzuki, Y.; Kageyama, M.; Morisawa, R.; Dobashi, Y.; Hasegawa, H.; Yokojima, S.; Kitagawa, O.

Chem. Commun. 51 (56), 11229-11232 (2015).

30. A comprehensive examination of the self-disproportionation of enantiomers (SDE) of chiral amides via achiral, laboratory-routine, gravity-driven column chromatography

Suzuki,Y.; Han, J.; Kitagawa, O.; Aceña, J. L.; Klika, K. D.; Soloshonok, V. A.

RSC. Advances 5, 2988-2993 (2015).

31. Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

Suzuki, Y.; Takahashi, I.; Dobashi, Y.; Hasegawa, H.; Roussel, C.; Kitagawa, O.

Tetarahedron Lett. 56 (1), 132-135 (2015).

32. Asymmetric Synthesis of Atropisomeric Compounds with an N-C Chiral Axis.

Isao Takahashi, Yuya Suzuki, Osamu Kitagawa

Org. Prep. Proc. Int. 46, 1-23 (2014). (Invited Review)

33. Chiral initiator-induces self-disproportionation of enantiomers via achiral chromatography: application to enantiomer separation of racemate

Tateishi, K. Tsukagoshi, S.; Nakamura, T.; Watanabe, S.; Soloshonok, V. A. Kitagawa, O.

Tetarahedron Lett. 54 (38), 5220-5223 (2013).

34. Unique Structural Property of 2,4,6-tri-tert-butylanilide: Isomerization and Switching between Separable Amide Rotamers through the Reaction of Anilide Enolates

Tsukagoshi, S.; Ototake, N.; Ohnishi, Y.; Shimizu, M. Kitagawa, O.

Chem. Eur. J. 19 (21), 6845-6850 (2013)

35. Rotational Isomerism in 2,4,6-tri-tert-butylanilides

Ototake, N.; Takahashi, I.; Tsukagoshi, S.; Maeda, T.; Kitagawa, O.

Tetrahedron, 69 (3), 1013-1016 (2013)

36. Catalytic Enantioselective Synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N-C chiral axis.

Takahashi, I.; Morita, F.; Kusagaya, S.; Fukaya, H.; Kitagawa, O.

Tetrahedron: Asymmetry, 23 (24), 1657-1662 (2012)

37. Studies on Rotational Barriers of N-C Axially Chiral Compounds: Increase in the Rotational Barrier by Aromatization.

Suzumura, N.; Kageyama, M.; Kamimura, D.; Inagaki, T.; Dobashi, Y.; Hasegawa, H.; Fukaya, H.; Kitagawa, O.

Tetrahedron Lett. 53 (33) 4332-4336 (2012).

38. Enantiomer Self-disproportionation of Non-racemic Chiral Amine Derivatives through Achiral Chromatography.

Nakamura, T.; Tateishi, K.; Tsukagoshi, S.; Hashimoto, S.; Watanabe, S.; Soloshonok, V.; Acena, J. L.; Kitagawa, O.

Tetrahedron, 68 (21) 4013-4017 (2012)

39. Self-disproportionation of enantiomers via achiral chromatography: a warning and an extra dimension in optical purifications.

Vadim Soloshonok, Christian Roussel, Osamu Kitagawa and Alexander Sorochinsky

Chem. Soc. Rev. 41 (11), 4180 - 4188 (2012)

40. Notable Structural Property of 2,4,6-Tri-tert-butylanilide Enolates: Interconversion between the Rotamers and Their Reactivity.

Ohnishi, Y.; Sakai, M.; Nakao, S.; Kitagawa, O.

Org. Lett. 13 (11) 2840-2843 (2011).

41. 炭素-窒素不斉軸を有する新規アトロプ異性化合物の触媒的不斉合成と不斉反応への応用

高橋昌志，北川　理

有機合成化学協会誌　69(9) 985-993（2011）.

42. Intramolecular Diels-Alder reaction of N-allyl 2-furoyl amides: effect of steric strain and amide rotational isomerism.

Nakamura, M,; Takahashi, I.; Yamada, S.; Dobashi, Y.; Kitagawa, O.

Tetrahedron Lett. 52 (1) 53-55 (2011).

43. Catalytic Enantioselective Synthesis of Atropisomeric Indoles Having an N-C Chiral Axis.

Ototake, N.; Morimoto, Y.; Mokuya, A.; Fukaya, H.; Shida, Y.; Kitagawa, O.

Chem. Eur. J. 16 (23) 6752-6755 (2010).

44. Atropisomeric Lactam Chemistry: Catalytic Enantioselective Synthesis, Application to Asymmetric Enolate Chemistry and Syntesis of Key intermediates for NET inhibitors.

Takahashi, M.; Tanabe, H.; Nakamura, T.; Kuribara, D.; Yamazaki, T.; Kitagawa, O.

Tetrahedron 66 (1), 288-296 (2010).

45. Highly Selective Stereodivergent Synthesis of Separable Amide Rotamers Using Pd Chemistry and Their Thermodynamic Behaviors.

Ototake, N.; Nakamura, M.; Dobashi, Y.; Fukaya, H.; Kitagawa, O.

Chem. Eur. J. 15 (20), 5090-5095 (2009).

46. Stereoselective Synthesis of Separable Amide Rotamers Using π-Allyl-Pd Catalyst and Their Thermodynamic Behavior.

Ototake, N.; Taguchi, T.; Kitagawa, O.

Tetrahedron Lett. 49, 5458-5460 (2008).

47. Catalytic Enantioselective Synthesis of Key Intermediates for NET Inhibitors using Atropisomeric Lactam Chemistry.

Kitagawa, O.; Kurihara, D.; Hajime, T.; Shibuya, T.; Taguchi, T.

Tetrahedron Lett. 49 (3), 471-474, (2008) Cover Figure Article に選定.

48. Highly Enantioselective Synthesis of Atropisomeric Anilide Derivatives through Catalytic Asymmetric N-Arylation: Conformational Analysis and Application to Asymmetric Enolate Chemistry.

Kitagawa, O.; Yoshikawa, M.; Tanabe, H.; Morita, T.; Takahashi, M.; Dobashi, Y.; Taguchi, T.

J. Am. Chem. Soc. 128 (39), 12923 - 12931, (2006).

49. Catalytic Asymmetyric Desymmetrization of meso-Diamide derivatives through Enantioselective N-Allylation Using Chiral π-Allyl Pd Catalyst: Improvement and Reaversal of the Enantioselectivity.

Kitagawa, O.; Matsuo, S.; Yotsumoto, K.; Taguchi, T.

J. Org. Chem. 71 (6), 2524-2527, (2006). Synfacts誌にハイライト

50. Efficient Synthesis of Optically Active Atropisomeric Anilides through Catalytic Asymmetric N-Arylation Reaction.

Kitagawa, O.; Takahashi, M.; Yoshikawa, M.; Taguchi, T.

J. Am. Chem. Soc. 127 (11), 3676-3677, (2005). 一般向け月刊誌“化学”に注目論文としてハイライトされた.

51. Catalytic Asymmetric Synthesis of Vicinal Diamine Derivatives through Enantioselective N-Allylation using Chiral π-Allyl Pd-Catalyst.

Kitagawa, O.; Yotsumoto, K.; Kohriyama, M.; Dobashi, Y.; Taguchi, T.

Org. Lett., 6 (20), 3605-3607, (2004).

52. Iodine Atom Transfer [3+2] Cycloaddition Reaction with Alkenes Using Unsymmetrical Allylated Active Methine Radicals.

Kitagawa, O.; Miyaji, S.; Sakuma, C.; Taguchi, T.

J. Org. Chem. 69 (7), 2607-2610 (2004).

53. Synthesis of Optically Active Atropisomeric Anilide Derivatives through Diastereoselective N-Allylation with a Chiral Pd-π-Allyl Catalyst.

Kitagawa, O.; Takahashi, M.; Kohriyama, M.; Taguchi, T.

J. Org. Chem. 68 (25), 9851-9853 (2003).

54. Radical Iodine Atom Transfer [3+2] Cycloaddition Reaction with Electron-rich Alkenes using N-Tosyl Iodoaziridine Derivatives as Novel Azahomoallyl Radical Precursors.

Kitagawa, O.; Miyaji, S.; Yamada, Y.; Fujiwara, H.; Taguchi, T.

J. Org. Chem., 68 (8), 3184-3189 (2003).

55. Catalytic Asymmetric Synthesis of Optically Active Atropisomeric Anilides through Enantioselective N-Allylation with Chiral Pd-tol-BINAP Catalyst.

Kitagawa, O.; Kohriyama, M.; Taguchi, T.

J. Org. Chem. 67 (24), 8682-8684 (2002).

56. Radical Cascade Reaction with 1,4-Dienes and 1,4-Enynes using 2-(Iodomethyl)cyclopropane-1,1-dicarboxylate as a Homoallyl Radical Precursor: One-step Synthesis of Bicyclo[3.3.0]octane Derivatives.

Kitagawa, O.; Yamada, Y.; Fujiwara, H.; Taguchi, T.

Org. Lett. 4 (6), 1011-1013 (2002).

57. Radical [3+2]-Cycloaddition Reaction with Various Alkenes Using Iodomethylcyclopropane Derivatives as New Homoallyl Radical Precursors.

Kitagawa, O.; Yamada, Y.; Fujiwara, H.; Taguchi, T.

J. Org. Chem. 67 (3), 922-927 (2002).

58. Iodoaziridine Derivatives as Novel Azahomoallyl Radical Precursors for [3+2] Cycloaddition Reactions with Alkenes.

Kitagawa, O.; Yamada, Y.; Fujiwara, H.; Taguchi, T.

Angew. Chem., Int. Ed. 40 (21), 3865-3867 (2001).

59. Radical [3+2] Cycloaddition Reaction with Alkenes using Dimethyl 2-Iodomethylcyclopropane-1,1-dicarboxylate as a New Homoallyl Radical Precursor.

Kitagawa, O.; Fujiwara, H.; Taguchi, T.

Tetrahedron Lett. 42 (11), 2165-2167 (2001).

60. Synthesis of Optically Active Aldol Derivatives through Chilarity Transfer Type 1,2-Wittig Rearrangement of α-Alkoxycarboxamides.

Kitagawa, O.; Momose, S.; Yamada, Y.; Shiro, M.; Taguchi, T.

Tetrahedron Lett. 42 (29), 4865-4867 (2001).

61. 光学活性アトロプ異性アニリド誘導体の合成と不斉反応への応用：

北川　理，田口武夫

有機合成化学協会誌 59 (7), 680-688 (2001).

62. Intramolecular Carbostannation Reaction of Active Methine Compounds with an Unactivated C-C π-Bond Mediated by SnCl4-Et3N

Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T. Shiro, M.

J. Org. Chem. 65 (21), 6819-6825 (2000).

63. Stereoselective Synthesis of Diastereomeric Atropisomeric Lactam with Various Ring Sizes and Their Structural Characterization.

Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi. T.

Tetrahedron Lett. 41 (44), 8539-8544 (2000).

64. Synthesis of Optically Active 5-Substituted-2-pyrroridinone Derivatives Having Atropisomeric Structure and 3,5-Cis-selective Reaction of Their Enolates with Electrophiles.

Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T.

J. Org. Chem. 65 (4), 1108-1114 (2000).

現在までの査読論文の累計　106報 

1. A unique method for highly enantioselective synthesis of N-C axially chiral compounds.

Osamu Kitagawa

Chem, 7, 1696-1698 (2021)

2. 触媒的不斉芳香族アミノ化反応を利用する炭素−窒素軸不斉化合物の効率的合成

北川　理

薬学研究の進歩，研究成果報告集25, 15-20 (2009).

3. ヨードメチルシクロプロパン誘導体を用いるヨウ素原子移動型ラジカル[3+2]付加環化反応：　北川　理，田口武夫

FIU Letters，６月（第７号），1-4 (2006).

4. 新規ヨード環化反応ならびにラジカル付加環化反応の開発

北川　理， 田口武夫

TCIメール，number 121, 1-15 (2004).

5. Iodocarbocyclization and Intramolecular Carbometalation Strategies for Carbocycles.

Takeo Taguchi and Osamu Kitagawa:

有機合成　創造の軌跡　ー126のマイルストーンー　有機合成化学協会編，2002, pp 202-203.

1.  2023年度長瀬科学技術振興財団 研究助成 250万円 （単独，直接経費）

炭素-窒素軸不斉キナゾリノンを基本骨格とする同位体アトロプ異性分子の創製 

2. 科研費　2023-2025年　基盤研究 (C) ３6０万円（単独，直接経費）

炭素-窒素軸不斉チオアミド の触媒的不斉合成と不斉反応への応用

3. 科研費　2020-2022年　基盤研究 (C) ３３０万円（単独，直接経費）

オルト位に極小置換基を有する炭素-窒素軸不斉化合物の創製

4. 科研費　2017-2019年　基盤研究 (C) ３７０万円（単独，直接経費）

生理活性炭素-窒素軸不斉キナゾリノンの触媒的不斉合成と構造特性

5. 科研費　2014-2016年　基盤研究（C）３９０万円（単独，直接経費）

エナンチオ選択的異性化を利用する光学活性炭素-窒素軸不斉アミンの合成

6. 科研費　2010-2012年　基盤研究（C）３5０万円　（単独，直接経費）

非アミド型炭素−窒素軸不斉化合物の触媒的不斉合成と不斉反応への応用

7. 大鵬薬品工業受託研究費　2009−20012年　３６０万円　（単独，直接経費）

光学活性フェネチルアミンの効率的合成法の開発に関する研究

8. 科研費　2006-2008年　基盤研究（C）３5０万円　（単独，直接経費）

触媒的不斉芳香族アミノ化反応を利用する光学活性含窒素化合物の効率的合成

9. 薬学研究奨励財団研究助成金 2005年度　１００万円 （単独）

触媒的不斉芳香族アミノ化反応を利用する炭素-窒素軸不斉化合物の効率的合成

10. 科研費　2002-2004年度　基盤研究（C）３４０万円　（単独）

窒素ラジカルの新規発生方法の開発と分子間付加環化反応への応用に関する研究

11. 科研費　2000-2001年度　奨励研究 (A) ２３０万円　（単独）

非ビアリール型軸不斉アニリドのエナンチオ選択的合成と不斉反応への応用に関する研究